Tri-o-tolylphosphine → Ammonia

Participants

Reaction Steps

(3R)-3-[2-(benzyloxy)-5-bromophenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Prepared according to WO1994/11337, 800 mg, 1.66 mmol), tert-Butyl{2-[4-(allyloxy)phenyl]ethyl}carbamate (Preparation 5, 924 mg, 3.33 mmol), palladium acetate (37 mg, 0.16 mmol), tri(o-tolyl)phosphine (101 mg, 0.33 mmol), and diisopropylethylamine (435 ul, 2.50 mmol) were heated at 90° C. in acetonitrile (10 ml) under a nitrogen atmosphere for 12 hours. The reaction was cooled to room temperature and poured onto ethyl acetate (30 ml) and water (20 ml). The organics were separated, washed with saturated aqueous sodium hydrogen carbonate (20 ml), water (20 ml), brine (20 ml), dried (magnesium sulphate) and the solvent removed in vacuo, the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (90/10/1.0 by volume) to furnish the title compound as a glass, 475 mg.

Provenance & Evidence